


Five Times Deadpool Asked Spider-Man For Relationship Advice and One Time He Took It

by kangaroar



Category: Deadpool - All Media Types, Marvel, Marvel Cinematic Universe, Spider-Man - All Media Types
Genre: 5+1 Things, Confusion, Cute, Cutesy, Developing Relationship, Drabble, Falling In Love, First Dates, Flirting, Fluff, Fluff and Angst, Friends to Lovers, Getting Together, Happily Ever After, Happy Ending, Humor, Identity Porn, Idiots in Love, Insecurity, Jealousy, Love Confessions, M/M, Mutual Pining, One Shot, Pre-Relationship, Romance, Secret Identity, Sweet, Teasing, and as a result gets super jealous but he's still wade's friend so he tries to help anyway, basically peter feels like wade replaced him
Language: English
Status: Completed
Published: 2018-07-02
Updated: 2018-07-02
Packaged: 2019-06-01 02:13:18
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,248
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15132830
Author URL: https://archiveofourown.org/users/kangaroar/pseuds/kangaroar
Summary: Deadpool has found a new mystery love interest. For some reason, Spider-Man doesn't like this development at all.





	Five Times Deadpool Asked Spider-Man For Relationship Advice and One Time He Took It

**Author's Note:**

> hehehe i wanted to try the 5+1 trope
> 
> also i uploaded twice in one day!!! aren't u guys proud 
> 
> please enjoy!!

The first time Deadpool asked Spider-Man for relationship advice was when he ambushed Spider-Man at 7 P.M. atop a Manhattan skyscraper with four bags of tacos, two in each hand.

“Baby boy!” An unmistakable voice called out from behind Spider-Man, startling him.

Spider-Man groaned, slapping a hand to his face and dragging it down his mask. “Not you,” he mumbled through gritted teeth. He _really_ wasn’t in the mood to be dealing with Deadpool’s incessant chatter today. He–or rather, Peter– was a day behind on his physics assignments, he had a mechanical engineering project due by the end of the week that was worth about a third of his total grade, and he hadn’t started on any of them.

Sometimes Spider-Man really wished that he was just plain old Peter Parker again.

“What do you _want?”_ he ground out in an annoyed tone, but Deadpool didn’t seem fazed in the slightest by it.

“What do you mean, sweet cheeks? It’s Taco Tuesday! Don’t tell me you’re gonna ditch me _again,”_ Deadpool whined, drawling out the last word in a sickly sweet manner that made Spider-Man want to explode.

“No time,” Spider-Man told him. He bit back a sigh after a moment of guilt, knowing that it wasn’t really Deadpool that was pissing him off. It was just the mountain of stress and homework assignments piled high on his shoulders. “Don’t you have somewhere to be and someone to un-alive, anyway?”

Deadpool pouted. The depth of his facial expressions that he managed to convey through his mask never failed to amuse Spider-Man (but he would never admit that). “I stopped un-aliving, remember? Damn, I thought you’d have at least a _little_ faith in me. You lectured me so many times on the ‘ _importance of human life_ ’ I thought I was gonna shoot myself. But then that would be un-aliving, so I didn’t.” Deadpool paused thoughtfully. “Whoa… that’s annoyingly paradoxical. Baby boy, you saved my life! But not really, I guess since I can’t die… but also you were the thing that made me want to die, so what the hell? Did you save me or almost kill me?”

Spider-Man stared at Deadpool as he continued his one-sided conversation before sitting down on the edge of the building with a resigned sigh, grabbing one of the bags of tacos from Deadpool’s hand. “Shut up and eat the tacos.”

“Don’t boss me around, that’s one of my turn-ons.” Deadpool winked at Spider-Man before sitting down next to him, close enough that their thighs touched and Spider-Man’s nose was hit by the faintest whiff of Mexican food, gunpowder, and something vaguely sweet. “So how’s it hanging? Pretty good lately?”

“You could say that,” Spider-Man scoffed. “Apparently finals week is prime time for criminals to come out of their caves.” Vaguely, he wondered if Deadpool remembered that he was a student.

“Aw, stressed, baby boy? You know, I know a _surefire_ way to-“

“Shut up.” He tried to sound stern and unamused, but he couldn’t quite stifle the smile that rose to his lips. Apparently, Deadpool noticed, because he started smiling too. A flurry of quips and comebacks rose to Spider-Man’s lips to counter the inevitable flood of teasing and flirting from Deadpool, but he was surprised when Deadpool seemed to change the subject.

“It’s been pretty good on my end too.” His voice almost sounded… dreamy?

“Really? How so?” Spider-Man cocked his head interestedly, watching as Deadpool turned his face away and lifted his mask, quickly inhaling an entire taco before lowering the mask and facing Spider-Man again. It saddened him slightly whenever Deadpool’s insecurities rose to his surface in moments like that.

“There’s this guy I’m kind of getting attached to and I think he’s getting attached to me too and he’s so cute and his ass is out of this world–not anymore than yours is, though, Spidey, don’t worry– and he’s so adorable and he’s funny and nice and smells good and–“

Spider-Man listened as Deadpool babbled, each word casting a darker and darker shadow over his mind. He shrugged it off, chalking it up to stress. “What’s his name?”

“Jealous?” Deadpool raised his eyebrows at Spider-Man, who rolled his eyes. “Actually, this brings me back to the whole entire point of this meeting–“

“I thought the point of this meeting was Taco Tuesday,” Spider-Man interrupted, feeling slightly annoyed for a reason he couldn’t quite place.

“–oh, well that too, but I wanted to ask you what you think a good location for a first date would be!”

Spider-Man felt the annoyance running through his veins increase by tenfold. “Why would you ask me? I haven’t had a date in years.”

“Come on, you’re a New York native!” The fact that Deadpool ignored the last statement, rather than flirting as he usually would, made Spider-Man even angrier. He decided that he must have been _extremely_ hangry and said the first thing that popped into his head just to get Deadpool out of his hair as fast as he could so he could go home and eat. Hopefully that would improve his mood.

“The Hall of Science.”

“Oh, you’re so right! He’s a complete nerd so he’ll love it!” Deadpool pulled out a pen and a tiny notepad from one of his thigh holsters to scribble something down before realizing it had no ink. After looking frantically around in his many other pouches and holsters, he stuck a finger into a taco and wrote something in taco sauce before downing the taco and standing up. “Thanks, Spides! Always knew I could count on you.” Deadpool winked before jumping off the side of the building, leaving Spider-Man confused and alone.

‘ _Aunt May always says I’m a nightmare when I haven’t eaten,’_ he thought numbly, before noticing that he was still holding Deadpool’s bag of tacos.

The irony only annoyed him even more. 

* * *

 

The second time Deadpool cornered Spider-Man was approximately two weeks after their first encounter.

“Spidey!” Deadpool eagerly poked his head through the door of the café, the bells hanging above the door jingling lightly. “Fancy meeting you here!”

“Hi, Deadpool.” Spider-Man had already almost forgotten the tension of their earlier run-in, lifting his mask to eat a bite of his pancakes. Almost.

“Pancakes at 12 A.M.? You’re a man after my own heart,” Deadpool grinned, sitting across from Spider-Man. “Where ya been lately? I missed you.” Deadpool sniffled, almost half-convincingly.

“I hung out in Queens for a bit. Crime rate shot up.” It was most _definitely_ not because he was avoiding Deadpool, and he if he was avoiding him, it _definitely_ wasn’t because of that ugly, jealous beast that had awoken inside of him after their last meeting.

“Fight anyone cool?”

“Ehh. Electro stirred some shit up one night, but nah, nothing that interesting.”

“Shame. Nothing’s really been going on in Manhattan either.” Deadpool sighed and propped his head on his hand, elbow resting on the table. “You should come back. I miss you. You’re the only person who knows how to have fun within a 500 mile radius of Stark Towers.”

Spider-Man rolled his eyes, even though Deadpool couldn’t see. “You don’t mean that.”

“Of course I do! Every day, I look out my bedroom window, waiting for my favorite webslinger to swing into my room and tie me up and–“

“Don’t you have a boyfriend now or something?” Spider-Man tried his hardest _not_ to sound interested in any way, but if the tiny smile playing on Deadpool’s lips was any indication, he failed miserably.

“He’s not my boyfriend _yet_ ,” Deadpool said, almost gloatingly. “He’s a work in progress.”

“Hmm.” Spider-Man picked at his pancakes even though he’d only taken a few bites. “How was the Hall of Science?” Why was he asking? He didn't even care. At least, he didn't  _want_ to care.

Deadpool shrugged. “Pretty good. Actually, this was an _excellent_ segue into the main reason why I wanted to find you–“ Spider-Man immediately bristled at that “–besides the fact that I missed you, of course, but I wanted to ask you how you’d preferred to be wooed.”

“Why are you asking me?!” Spider-Man all but shouted. God, he was  _so tired_ of the fact that Deadpool was only seeking him out to ask for relationship about some guy that he didn't even know, and he was  _so tired_ that he was even upset about it when he knew he shouldn't have been.

“I dunno,” Deadpool mused, seeming unbothered at Spider-Man’s raised voice. “I feel like he’d probably be really similar to you, ya know? He’s kinda broody, he likes his distance, he plays hard to get, he has a _really_ nice butt, stuff like that.”

Spider-Man felt his blood turn to ice, but he kept his cool. He closed his eyes, trying to silence the part of his brain that whispered to him that he'd  _been replaced_.

“Anyway,” Deadpool continued, “I just wanted to know what you’d like if I was trying to woo you. Like, obviously the continued taco dates didn’t work, and I didn’t peg you for a flower kind of guy, and I just don’t know if you’re more of a slow, romantic kind of guy or a dirty, straight-to-the-point kind of guy, you know?”

Spider-Man sighed and put his fork down with a clatter, rubbing his temples. “Probably slow and romantic. That seems much less inflammatory than dirty, at least, especially if you don’t know the guy that well yet.”

Deadpool sighed once more. “Ugh, time to spend another paycheck on flowers and chocolates, am I right? Thanks for your input. Later, Spidey!” Deadpool picked up Spider-Man’s fork, took a giant bite of his pancakes at light speed, and then left the café with a wave.

Spider-Man picked up the fork with mild annoyance, wiping the prongs with his napkin. His annoyance slowly gave way to dejection as he replayed the conversation in his head.

‘ _What do you mean, the taco dates didn’t work…?’_

* * *

 

The third time Spider-Man ran into Deadpool was actually planned. After a week or so after Deadpool had eaten Spider-Man’s pancakes at the café, Spider-Man decided that he was done with letting Deadpool play with his emotions.

So obviously, the solution was to spend _more_ time with him. Because then Spider-Man could rest easy in knowing that Deadpool was no longer controlling his patrol patterns, or what he thought about every night before he went to sleep.

He had texted Deadpool the night before, asking for a team-up, to which Deadpool had _very_ enthusiastically accepted, which led had led to them meeting up in their favorite patrol spot in the state: Lexington Avenue. Lots of shady criminals, alleyways, druggies, vulnerable prostitutes… it was crime central, so there was no way that they would be bored.

Except, somehow, they had begun their patrol at 11 in the evening and it was currently 2 in the morning. And, somehow, there hadn’t been a single instance of crime on Lexington, nor in a five mile radius of where they had stationed themselves. So for the past three hours Spider-Man had begun to go deaf from the sheer amount of how much Deadpool had talked into his ear, proving himself once again of being able to hold one-sided conversations with himself for literal days.

Spider-Man groaned and shut his eyes, welcoming the cool breeze of the evening that eased the hot, practically airtight suit as Deadpool blabbered into his ear. He’d long since tuned Deadpool out, but here and there he caught wind of things about Deadpool’s current mercenary projects, his annoyance at the uselessness of the NYPD, and his frustration at the government’s treatment of superheroes and vigilantes. Spider-Man was midway through a yawn when something finally caught his attention.

“The dates with that guy haven’t been going so well.” Spider-Man caught a rueful smile playing at Deadpool’s lips.  
“What’s been going on?” Spider-Man asked, trying to suppress the entirely unreasonable swell of relief in him.

“I dunno, I’ve been feeling like maybe the hard to get attitude might just be that he doesn’t want me.” Deadpool looked rejected for a moment, an uncharacteristic weight seeming to settle on his shoulders. It almost made Spider-Man wince to see him look so discouraged.

“If he’s anything like me, I don’t think he means to act like he’s rejecting you,” Spider-Man offered. “He’s probably just confused about how he feels and he’s probably just overanalyzing everything and taking it out on you, you know? And I’ve never met anyone even remotely like you, so I’m guessing that he just doesn’t know how to deal with your personality just yet. I’m sure he doesn’t mean it.” He didn’t really know why he was now _helping_ Deadpool with this mystery love interest– it was the complete opposite of his actions before.

“I dunno, baby boy,” Deadpool mumbled, and the use of the nickname made Spider-Man’s heart jump. It had been so long since Deadpool had called him that. “It’s not too hard to see why he wouldn’t like me.”

“Shut up,” Spider-Man said without thinking. “I know that your moral code isn’t the same as everyone else’s, but your heart is the same. He should be able to see that.”

Deadpool rolled his head back and let out a small, sad puff of breath. “Why would he when no one else does?”

“I do!” Spider-Man exclaimed. “Why else would I hang out with you all the time? Man, maybe this kid isn’t doing anything wrong, maybe _you’re_ just thick-skulled–“

Deadpool laughed, interrupting his train of thoughts.

Spider-Man froze. For once, it wasn’t teasing or forced or crazed or malicious or restrained like it usually was. It rumbled from deep within his chest, its timbre making Spider-Man’s hairs stand on end. And it made him want to smile, too.

“Thanks, Spidey. You always know how to cheer me up.” Deadpool clapped a gloved hand onto Spider-Man’s shoulder. “Knowing how smart you are, you’re probably right, too.”

Spider-Man nodded at him, but his mind was already far gone. Suddenly he felt a wave of remorse for all the times he’d been curt, harsh, and downright cold to the mercenary, who had laughed it off every time. But as he played the sound of Deadpool laughing in his head over and over the flutter of Spider-Man’s heart began to drown out everything else around him.

* * *

 

The fourth time Deadpool contacted Spider-Man in regards to his budding relationship wasn’t actually to ask for advice, which surprised Spider-Man. Instead, when he arrived at their usual meeting place for Taco Tuesdays, he found Deadpool nowhere in sight except for a small letter in a white envelope at the place where Deadpool usually sat on the edge of the roof.

Spider-Man rolled his eyes at how much faith Deadpool had put into the wind not blowing the letter away.

He sat down and opened the letter, feeling unusually nervous.

‘ _Hey Spidey,_

_Job came up. Couldn’t refuse the offer (no, not for money reasons, this guy is just really bad and will fuck shit up for more people if I didn’t deal with him). Hope you understand. There’s a fifty included in the envelope in case you were hungry anyway. Also, thanks for helping me out with that guy I’ve been seeing. I think it’s finally starting to work out._

_You’re still my number one._

_And I’m still your number one fan._

_-DP’_

Spider-Man fished around in the envelope briefly before pulling out the promised fifty dollars. He rolled his eyes even harder at the fact that Deadpool had just _left_ an envelope with fifty dollars on the roof of a taco shop in the middle of downtown Manhattan on a windy evening. Maybe the mercenary had a stroke of luck about him or something.

Spider-Man stared at the money for a few seconds longer before putting the bill, along with the note, back inside the envelope. Deadpool’s apartment was a quick swing away and when he got to the building he scaled the side, prying open Deadpool’s window and leaving the envelope on the bedside table. He rummaged about the room until he found a writing utensil– one red Crayola crayon. He turned the envelope over and wrote a short message before putting the crayon back where he found it, slipping through the open window, and shutting it carefully behind him.

‘ _You’re welcome._

_-SM’_

* * *

 

The fifth time Deadpool talked to Spider-Man was when they were getting lunch together at a sandwich shop in Times Square. Nobody really commented about their suits, since usually people just assumed that they were a couple of cosplayers, which Spider-Man was grateful for.

“So what did you need help with?” Spider-Man asked, taking a large bite of his BLT.

“Well, I kinda sorta need help with how to pop the question, ya feel?” Deadpool fiddled with his thumbs, not meeting Spider-Man’s eyes.

Spider-Man all but choked. “You’re asking him to marry you already?!”

“No, dumbass!” Deadpool scoffed. “I’m asking him to be my boyfriend!”

“Oh, Jesus, I was gonna have a heart attack on behalf of the poor guy. I thought you guys were already a thing?” The beast insider Spider-Man had calmed down after their last two interactions, jealousy giving way to a desire to help his friend find happiness. But sometimes it still reared its head, no matter how much he tried to hide it.

“Not officially. But I’m trying to make it official, obviously.” Dadpool inhaled one of his sandwiches and grabbed one more from his pile. “I’ve never really had to ask before, surprisingly.”

Spider-Man chewed thoughtfully. “How’s he been reacting to your advances so far?”

“Pretty well. He’s still a nerd and I’m pretty sure he’s just confused in general about being so in love with someone so perfect,” Deadpool waggled his eyebrows, an impressive feat underneath the heavy leather and spandex of his mask, “but I think he’s beginning to warm up to me. Actually, he’s been reciprocating too.”

Spider-Man couldn’t help the slight pang of jealousy in his chest at the words. “That’s good. Do you think he’d say yes to being your boyfriend?”

“I mean, how could he resist?!” Deadpool bit off half of a pork roast sandwich in one mouthful. “I'm pretty sure, in all honesty, that he’s head over heels. He just doesn’t like admitting it. I just need to know how _you_ would want to be asked. I think that would give me a pretty good idea.

Spider-Man shrugged. “I’d probably want it to be pretty straightforward. I really dislike it when people beat around the bush, since I hate having my time wasted. So I’d just go straight to the point and take him to a nice place and ask straight up, you know?”

“But like, should I go traditional ‘Will you be my boyfriend?’ or should I go Deadpool ‘Your ass is outta this world and I’d like to wake up with it in my hands every morning from this point on?’”

Spider-Man rolled his eyes. “Find a happy medium. Unless you think he’d like any one approach more than the other.”

Deadpool smirked at Spider-Man. “Which one would you prefer?”

“Hmm…” Spider-Man hummed thoughtfully. “Honestly, I hate to say it, but probably the Deadpool approach. I would like the humor.”

“Good to know. Thanks as always, sweet cheeks.”

Spider-Man huffed good-naturedly. “Can’t be calling me that now that you’re about to have a boyfriend, can you?”

“Like I said before,” Deadpool said, the white eyes in his mask almost seeming to soften as he looked at Spider-Man, “you’re still my number one.”

* * *

 

The next day, Spider-Man was abruptly awoken by his phone ringing. He groaned as he realized that he had slept in his suit, which was never a comfortable experience, and groaned even louder when he realized that the ringtone that was playing was Right Said Fred’s _I’m Too Sexy_ : the ringtone Deadpool had set just for himself so Spider-Man would know whenever it was Deadpool that was calling.

“Deadpool?” Spider-Man said blearily, picking up the call. “It’s like, 9 AM on a Saturday morning. What’s so important?”

“Spidey!” Spider-Man had to physically hold the phone further away from his ear at the volume of Deadpool’s voice. “You gotta come down here! There’s a _very bad purple man–“_

“Oh my God,” Spider-Man whispered, his mind going straight to the only purple Titan he could think of. “What did you do this time? Don't tell me you _seriously_ told Thanos that his chin looks like the heel of a Yeezy?!”

“That’s not important!” Deadpool sounded extremely out of breath, which wiped away all doubt in Spider-Man’s head of whether or not the call was a prank. “Okay, maybe, but the point is, I am in very big trouble and I need you here!”

“I’m coming!” Spider-Man wrenched his suit to cling the right way to his body and tightened his mask and opened the window, perching on the ledge and holding out his wrist to shoot a web. “Where are you?”

“Corona! 111th Street! Come quick!”

Spider-Man hung up the call and shot a web to the side of the nearest building. It struck him that the address sounded oddly familiar, but he couldn’t think about that when his friend, and his hometown, were in trouble.

He landed on 111th barely six minutes after receiving the call from Deadpool, walking up the block to see where Deadpool was. There didn’t seem to be any commotion at all, especially when Deadpool had claimed that he was fighting Thanos.

Spider-Man was just about to give up as he reached the end of the block when the front of the Hall of Science caught his eye. So that was why the address sounded so familiar. His jaw all but dropped when he saw the main entrance.

The entire side of the cylindrical main building was covered in roses arranged in the shape of a heart, in the middle of which were the two letters “S” and “M”. People on the street had begun to notice, taking pictures and staring at the not-so-ambiguous message. Spider-Man scanned the street for Deadpool and nearly screamed as Deadpool landed behind him and touched his shoulder.

“Deadpool!” Spider-Man shouted. “What the hell is this?! I thought you were actually in trouble–“

Deadpool chuckled. “No, I wasn’t in trouble. But I wasn’t lying when I said I needed you.”

“Okay, but that doesn’t exactly explain the roses and my initials and _holy shit_ you just vandalized the Hall of Science–“

“Jesus, for someone that’s so smart, you can actually be pretty dumb sometimes. Why do you think I kept asking you for relationship advice? For someone I never actually named that I was trying to woo that was super duper suspiciously similar to _you?_ ” Deadpool clapped a hand to his forehead and shook his head.

Spider-Man was dumbfounded, both at the realization slowly dawning on him and the fact that he’d actually let Deadpool outsmart him for once. “… Oh.”

“Eloquent.” Deadpool laughed in the same way that had made Spider-Man’s heart flutter all those weeks ago. “So whaddya say, Spides? Are you gonna let me grab up on that ass for the rest of my life or what–“

Deadpool couldn’t finish the rest of his proposal because Spider-Man had clapped a hand to his mouth, silencing him. Spider-Man sighed, feeling the tension flow out of his shoulder like water and the dark cloud of jealousy that had resided in him since the beginning starting to dissipate.

“Yes.”

Deadpool’s mouth hung open slightly as Spider-Man released his hold, looking as though he was surprised. “Wait, seriously?”

“Why wouldn’t I say yes? Obviously, you could tell that I was into you, right?”

“Honestly, I was half expecting you to punch me in the face. I definitely didn’t expect you to be _that_ jealous when I first started messing with you.” Deadpool smirked.

“For that, I just might punch you.”

“No, don’t, that turns me on.”

Spider-Man sighed, but allowed the grin that he’d been suppressing to spread over his face. “Our first date as official boyfriends can be to clean up this mess you made,” he said, gesturing at the defaced museum. “Not that I don’t love it, of course,” he added as he noticed Deadpool’s shoulders beginning to slump.

“Man, if you think _this_ is vandalism, wait till you see what I did to all the billboards in the Square.”

Spider-Man could do nothing but laugh at that point. “Deadpool, you’re fucking crazy.”

“Crazy for you.” Deadpool walked closer to Spider-Man, putting his arms around Spider-Man’s shoulders. “Do I finally get that kiss I’ve always wanted?” he teased.

Spider-Man instinctively tipped his head to the side, as he’d always done when Deadpool had tried to kiss him as a prank in the past. “I don’t know if you deserve it, after the shit you pulled today,” he teased right back.

“Come on, Spider-Man,” Deadpool laughed.

Spider-Man smiled up at Deadpool, reaching behind his mask to undo the Velcro at the back. He hesitated a bit before he replied. “Peter.”

Deadpool stiffened. “Peter?”

Spider-Man nodded, his stomach full of butterflies as he reached behind Deadpool’s mask. Deadpool grabbed Spider-Man’s arms and lowered them, intertwining their fingers as he stared at him with the same softness in his eyes as the night before.

“Wade,” he said quietly.

Peter grinned as Wade leaned forward and finally pressed their lips together.

**Author's Note:**

> thank you for reading!


End file.
